What to Do When Skype4B Conversations Take Weeks to Appear in Outlook

You have a normal conversation in Skype for Business via Instant Messaging. The next day, you need to check the status of a task. You recall you mentioned this task in yesterday’s conversation. Better go check it in Conversation History.

Outlook is already open. You click the Conversation History folder and…wait, where’s the conversation? The last one you see is dated 2 weeks ago!

We ran up against this issue with a customer’s Skype for Business deployment. They had a server deployment, up and running since 2016. The Conversation History “delayed appearance” only started this past fall. Even more confusing, it didn’t occur for all users.

“I KNOW I talked to Beth yesterday…” Photo by rawpixel.com on Unsplash

The Cause: A Low Threshold for Conversation File Size

We checked all the obvious things, of course. But those were all clear. Only after testing & reviewing the Conversation History logs that did appear, followed by some MS research, did we find the cause.

Lync Server 2013 had an issue with long conversations. If a conversation’s history file ended up over 1MB in size, Lync Server could not upload the file to Exchange Server. This bug persisted into Skype for Business Server.

So if you end up having a long conversation with co-workers, plus a few images & documents shared around, your conversation grew past the server’s (tiny) 1MB limit!

The Solution: A Fix for Lync/Skype for Business Server, Then an Exchange Server Workaround

Microsoft did release a fix for this: KB3101496. It’s a security update issued November 10, 2015. Link to the update below.

Within the <appSettings> node, add the following line:<add key=”XmlMaxBytesPerRead” value=”1000000″ />

Restart your IIS server.

Again, wait a few hours. The conversations should start trickling into Conversation History, in groups of 10 or so. You may need to restart Outlook & the Skype for Business client a few times to get everything.

Sometimes Conversation Logs Delay Their Appearance. Call Them Out on Stage with These Fixes!

This is an issue which can fly under the radar. Our customer saw no error messages, and had no Outlook crashes related to it. They only noticed when someone did exactly what I portrayed earlier—tried to check a previous Skype4B conversation via their Outlook Conversation History.

Take a second to review your Outlook Conversation History. Hopefully this bug doesn’t affect you…but it doesn’t hurt to check!

Have you experienced a Conversation History “delayed appearance” in Outlook, or something similar?

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About the Skype for Business Insider Blog

The Skype4B Insider is a blog about the technology we use to communicate in business today. Here we talk about Microsoft's Skype for Business Server 2015, Lync Server 2013, Unified Communications, Voice over IP and related technologies like Exchange Server. Written by Chris W., MCSE in Communication and PlanetMagpie IT Consulting's Digital Marketing & Communications Manager.